Water → HCID 21710156, compound

HRID 650901Notes

Reaction equation

HRID 650901 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:13]([O-])=O)[C:5]1=[O:16])[CH3:3].O>CC(O)=O.[Fe]>[NH2:13][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH2:12][N:4]([CH:2]([CH3:3])[CH3:1])[C:5]2=[O:16]

Participants

5

Reactant 2

HCID 962WaterHCID 21710143HCID 21710143, compound

Product 1

HCID 21710156HCID 21710156, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 5.0 grams (0.022 mole) of 2-(1-methylethyl)-4-nitroisoindolin-1-one and 10 mL of water in 100 mL of HOAc was warmed to 50 C., and 5.0 grams of iron dust was slowly added. Upon completion of addition, the reaction mixture was stirred at 25 C. for about two hours, then it was filtered through diatomaceous earth. The filtrate was diluted with water and extracted with EtOAc. The organic layer was separated and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel using mixtures of EtOAc and methylene chloride as eluants. The fractions containing product were combined and concentrated under reduced pressure, yielding 3.6 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas warmed to 50 C
  2. additionUpon completion of addition
  3. filtrationit was filtered through diatomaceous earth
  4. additionThe filtrate was diluted with water
  5. extractionextracted with EtOAc
  6. customThe organic layer was separated
  7. dry with materialdried with magnesium sulfate
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated under reduced pressure to a residue
  10. customThe residue was purified by column chromatography on silica gel using mixtures of EtOAc and methylene chloride as eluants
  11. additionThe fractions containing product
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d98c51a06d64f79a394d79755ed6b80
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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